Technology Team Leader & Entrepreneur

What I've Learned After Failing at Hiring Several Times

2018, Dec 21 —
5 minute read

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I grew up around small businesses. My uncle has owned a machine shop for decades and my dad has been an entrepreneur since I was 9. I got interested in startups and small business myself when I was in college, and for the past few years, that’s what my career has been.

While I’ve obviously still got a lot to learn, I’m realizing that there are two fundamentals you must get right in any small business if you want it to grow:

People and Process.

I’ve been reading The E-Myth this month. It’s fantastic; if you’re an entrepreneur in any form, go buy or rent it - my used copy cost like $6.

One of the author’s key tenants is that small businesses should be run on a franchise model. As the founder, you should set up the processes that make the business run, and then hire people to carry them out. Once you know your process and you know how to turn $1 into $2 (or $3 or $5 or whatever), then you’ve got a business who’s only limit is your ambition.

This sounds good on paper, but people and process are both really hard to get right.

My Success With Process

When it comes to process, I feel good. I’m not the best software engineer, but I make up for my lack of detail orientation by being extremely process-driven. I don’t do anything without writing it down, so there’s always a trail of documentation for me to follow if I want to know how I did something.

I’m also pretty good at helping other people develop processes. I have run through a few iterations of process improvements at both of my last two jobs, so I’ve had several chances to improve and get things right. The opportunity to practice things is what makes you better; this includes practice setting up new processes.

Lately I’ve been setting up a new customer operations process for The Graide Network, and I really love it. I’ve been at this company since it was started, but I’m still learning finer points about how grading papers really works, how to work with college students, and what teachers expect from us. Anyway, when it comes to processes - setting them up and working within them - I feel good.

My Struggle With People

2018 has been a tough year for me the people side of things.

If you asked me a year ago if I thought I was good at hiring, I would have said yes, but my track record has proven otherwise. Three of my last four direct hires have left within a year of onboarding, and while I do still think I’m a decent people manager (because I’m better at the process stuff), I have been really bad at choosing the right people for our stage of business.

We’re hitting our stride at the Graide Network: sales are growing, we’re getting larger customers, and we were able to hire a couple really great non-technical people this year. That said, I’m now the only one doing engineering, and while I enjoy it, I’d rather be able to hand off most of the development and architecture to someone else. In order to do that, I’ve got to get better at hiring.

Reflecting on My Mistakes

As I close out 2018 and prepare to kick off a new hiring process in 2019, I wanted to document some of the mistakes I’ve made in regards to hiring. I know it’s not popular for a CTO to talk about why they suck at hiring, but I believe the only way to address a weakness is to acknowledge it and face it head on, so here goes:

I ignored blatant red flags because I was impatient

This was my biggest blunder by far. I hired a candidate who was 30 minutes late for an interview because he was so swamped at his current job. When I hired him, he was always “really busy,” but never focused or working on the right things. He worked a ton, but never got anything done.

I was focused on years of technical experience instead of initiative, learning speed, and potential

I passed on several high potential recent bootcamp grads because I wanted someone who had spent a couple years in the field. This seems reasonable, but what I got was someone who had spent many years in the field doing things the wrong way, so they came with a lot of bad habits that I had to try to break.

I engaged recruiters rather than talking to my network and waiting for the right referral

I did not have the right rubric for hiring

Finally, my rubric was full of technical prerequisites. I wanted someone who knew a specific set of languages and frameworks so I wouldn’t have to teach them a ton of stuff, but I passed on several candidates who were passionate about our mission but not aligned on technical skills. If someone is aligned on mission and passionate about the product, they’ll put in extra time to learn the tech stuff, plus what we’re doing isn’t that technically complex anyway.

In hindsight, every bad hire I’ve made seems obvious. I’m an engineer, and while I like process and management, I don’t like hiring, so I rush the process and put pressure on myself to pick someone even if I’m not sure. In addition, I was looking for people with the wrong sets of skills, and ignoring high potential learners who could come in and flex into any position we had. In truth, I’m not that good at this yet.

So, I’m writing this post mostly as a self-reflection and reminder. I want to get better at hiring, so I think it’s important that I catalog what I did wrong so that future me doesn’t make the same mistakes again. If people and process really are the most important parts of a startup, I have to get better at the people part.

What have you learned about hiring this year? I’m obviously looking for advice and feedback, so I’d love to hear your story. Find me on Twitter to keep the conversation going.